6533b871fe1ef96bd12d10d1

RESEARCH PRODUCT

Pauson-Khand reaction of internal dissymmetric trifluoromethyl alkynes. Influence of the alkene on the regioselectivity.

Nuria AiguabellaAntoni RieraXavier VerdaguerCarlos Del PozoElsa M Arce

subject

Ciclització (Química)EthyleneHydrocarbons FluorinatedStereochemistryNorbornadieneQuímica organometàl·licaPharmaceutical ScienceAlkynetrifluoromethylalkynesCrystallography X-RayArticlecyclopentenonesAnalytical ChemistryRing formation (Chemistry)cycloadditionslcsh:QD241-441chemistry.chemical_compoundlcsh:Organic chemistryDrug DiscoveryPhysical and Theoretical ChemistryNorbornenechemistry.chemical_classificationPauson-Khand reactionTrifluoromethylMolecular StructureAlkenePauson–Khand reactionOrganic ChemistryRegioselectivityStereoisomerismCobaltEthylenesNorbornaneschemistryOrganometallic chemistryChemistry (miscellaneous)AlkynesregioselectivityMolecular Medicine

description

Abstract: The scope of the Pauson-Khand reaction (PKR) of internal trifluoromethyl alkynes, previously described with norbornadiene, is expanded to norbornene and ethylene. A thorough structural analysis of the resulting PK adducts has been carried out to unveil that α-trifluoromethylcyclopentenones are preferred in all cases, independently of the electronic properties of the alkyne. The regioselectivity observed with norbornadiene and ethylene is higher than in the case of norbornene.

yearjournalcountryeditionlanguage
2014-02-03Molecules (Basel, Switzerland)
10.3390/molecules19021763https://pubmed.ncbi.nlm.nih.gov/24496269